Trifluoroacetic acid → (6S)-N-(5-Chloro-2-pyridinyl)-5-azaspiro[2.4]heptane-6-methanamine

HRID 536591Notes

Reaction equation

C(OC([N:8]1[C@H:14]([CH2:15][NH:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][N:18]=2)[CH2:13][C:10]2([CH2:12][CH2:11]2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:11]1[C:10]2([CH2:13][C@@H:14]([CH2:15][NH:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][N:18]=3)[NH:8][CH2:9]2)[CH2:12]1

Participants

Conditions

Temperature: 0 °C

Procedure

(S)-tert-butyl6-(((5-chloropyridin-2-yl)amino)methyl)-5-azaspiro[2.4]heptane-5-carboxylate Intermediate 60, 600 mg, 1.77 mmol) was dissolved in dichloromethane (10 ml) and cooled to 0° C., then trifluoroacetic acid (4 ml) was added. After 1 hour at 0° C. and 3 hours at room temperature the solution was evaporated, the residue re-dissolved in dichloromethane was washed with saturated NaHCO3 aqueous solution. The organic layers were dried (Na2SO4) and concentrated under vacuum. The crude was purified by silica gel column chromatography (CHCl3/MeOH=8/2). (S)—N-(5-azaspiro[2.4]heptan-6-ylmethyl)-5-chloropyridin-2-amine was obtained as light yellow oil (400 mg).

Workup

custom3 hours at room temperature the solution was evaporated
dissolutionthe residue re-dissolved in dichloromethane
washwas washed with saturated NaHCO3 aqueous solution
dry with materialThe organic layers were dried (Na2SO4)
concentrationconcentrated under vacuum
customThe crude was purified by silica gel column chromatography (CHCl3/MeOH=8/2)

Sources & evidence

ORD record: ord-10dd6b7c037e432f8cd8e4780626fb82
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859608B2

Reaction notes

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